Pests such as insects and arachnids are a constant irritation and threat to man. They injure and destroy plants, consume stored food supplies, damage useful organic materials such as wood and wool, directly set upon man and animals and invade their dwellings contributing to the spread of some of the most serious and harmful diseases. A major factor in the control of such pest organisms is the agrichemical. There is a continuing need for new agrichemicals to replace those to which pest organisms have become resistant. There is always a need for chemicals possessing greater activity or which are active against a broader variety of pests.
Organotin compounds have been found to be effective against a variety of arthropod pests [Blum, M. S., J. Econ. Entymol., Vol. 53, 445 (1960)]. Trialkyltin compounds, i.e. those with three (3) hydrocarbon radicals bonded to a tin atom, are known to be useful against certain species of arthropods. U.S. Pat. No. 3,264,177 discloses tricyclohexyltin compounds which effectively control arachnids, but not insects. Other trialkyltin compounds, e.g., those disclosed in U.S. Pat. No. 3,702,360 which are effective insecticides, possess high phytotoxicity.
Tetraorganotin compounds, those containing four (4) hydrocarbon groups bonded to the tin atom, have unexpectedly been found to possess biological activity. U.S. Pat. Nos. 4,138,483; 4,212,810; 4,212,885; 4,316,853 and foreign equivalents thereof commonly assigned to M&T Chemicals, Inc. disclose trimethyl substituted, tetraorganotin compounds in which the fourth carbon-tin bond is to a substituted phenyl, benzyl, or heterocyclic moiety. Included within the M&T patents are compounds of the formulae: ##STR1## where R.sub.1 is CO.sub.2.sup.- Y.sup.+, CO.sub.2 R.sub.4, SO.sub.2 OR.sub.5, SO.sub.2 R.sub.5, SO.sub.3.sup.- Y.sup.+, PO(OR.sub.5)OR.sub.6, or PO(R.sub.5)R.sub.6 ;
R.sub.2 and R.sub.3 are H, F, Cl, Br, I, aryl, OR.sub.4, SR.sub.5, NR.sub.6 R.sub.7, NR.sub.5 R.sub.6 R.sub.7.sup.+ X.sup.-, acetyl, CO.sub.2 H, CO.sub.2.sup.- Y.sup.+, CO.sub.2 R.sub.4, SO.sub.2 OR.sub.5, SO.sub.2 R.sub.5, SO.sub.3.sup.- Y.sup.+, PO(OR.sub.5)OR.sub.6, PO(R.sub.5)R.sub.6, or CN, with the proviso that both R.sub.2 and R.sub.3 cannot be H; PA1 R.sub.4 is C.sub.1 -C.sub.12 alkyl; PA1 R.sub.5, R.sub.6, and R.sub.7 are H or C.sub.1 -C.sub.12 alkyl; PA1 X.sup.- is bromide, iodide, bisulfate, acetate, or methyl sulfate; PA1 Y.sup.+ is alkali metal or ammonium; PA1 Z is ##STR2## or an aromatic mono- or bicyclic heterocyclic group wherein each ring contains 5 or 6 atoms including one or two hetero atoms selected from N, O, and S, provided that Z cannot be pyridyl, furyl, or thienyl when m is 0 and the heterocyclic groups must be free of active hydrogen; PA1 m is 0 or 1; and PA1 p is 1 or 2. PA1 m is 1 or 2. PA1 R.sub.3 is H, OCH.sub.3, C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.6 cycloalkyl optionally substituted with CH.sub.3 or OCH.sub.3, C.sub.1 -C.sub.3 alkyl optionally substituted with OCH.sub.3 or OC.sub.2 H.sub.5, or ##STR5## R.sub.4 is H, C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.6 cycloalkyl optionally substituted with CH.sub.3 or OCH.sub.3, C.sub.1 -C.sub.3 alkyl optionally substituted with OCH.sub.3 or OC.sub.2 H.sub.5, or ##STR6## or R.sub.3 and R.sub.4 may be taken together to form ##STR7## R.sub.5 is H or CH.sub.3 ; R.sub.6 is CH.sub.3 ; PA1 X is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 Y is O or NR.sub.7 ; PA1 Z is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.7 is C.sub.1 -C.sub.3 alkyl; PA1 m is 0 or 1; PA1 p is 2, 3 or 4; and PA1 q is 0, 1 or 2; PA1 (1) the total number of carbons in R.sub.3 and R.sub.4 is no greater than 20; PA1 (2) when either R.sub.3 or R.sub.4 is ##STR8## and the other is alkyl, the total number of carbons in R.sub.3 and R.sub.4 is no greater than 12; and PA1 (3) when R.sub.3 is OCH.sub.3, then R.sub.4 is H or C.sub.1 -C.sub.4 alkyl. PA1 R.sub.3 is H, OCH.sub.3, C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.6 cycloalkyl optionally substituted with CH.sub.3 or OCH.sub.3, C.sub.1 -C.sub.3 alkyl optionally substituted with OCH.sub.3 or OC.sub.2 H.sub.5, or ##STR10## R.sub.4 is H, C.sub.1 -C.sub.20 alkyl, C.sub.5 -C.sub.6 cycloalkyl optionally substituted with CH.sub.3 or OCH.sub.3, C.sub.1 -C.sub.3 alkyl optionally substituted with OCH.sub.3 or OC.sub.2 H.sub.5, or ##STR11## or R.sub.3 and R.sub.4 may be taken together to form ##STR12## R.sub.5 is H or CH.sub.3 ; R.sub.6 is CH.sub.3 ; PA1 X is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 Y is O or NR.sub.7 ; PA1 Z is H, F, Cl, CH.sub.3 or OCH.sub.3 ; PA1 R.sub.7 is C.sub.1 -C.sub.3 alkyl; PA1 m is 0 or 1; PA1 p is 2, 3 or 4; and PA1 q is 0, 1 or 2; PA1 (1) the total number of carbons in R.sub.3 and R.sub.4 is less than or equal to 20; PA1 (2) when either R.sub.3 or R.sub.4 is ##STR13## and the other is alkyl, the total number of carbons in R.sub.3 and R.sub.4 is less than or equal to 12; and PA1 (3) when R.sub.3 is OCH.sub.3, then R.sub.4 is H or C.sub.1 -C.sub.4 alkyl. PA1 (1) the compounds of Formula I wherein PA1 (2) compounds of preference (1) wherein X is H; PA1 (3) compounds of preference (2) wherein PA1 (1) 2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (2) N-methyl-2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (3) N,N-dimethyl-2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (4) N-butyl-2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (5) N-(1,1-dimethylethyl)-2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (6) N-ethyl-N-methyl-2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (7) N,N-dihexyl-2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (8) N-dodecyl-2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (9) N-phenyl-2-[(trimethylstannyl)methyl]benzenesulfonamide; PA1 (10) 4-[2-[(trimethylstannyl)methyl]phenylsulfonyl]morpholine; PA1 (11) 1-[2-[(trimethylstannyl)methyl]phenylsulfonyl]pyrrolidine; PA1 (12) N-methyl-4-[(trimethylstannyl)methyl]benzenesulfonamide; and PA1 (13) N,N-dimethyl-4-[(trimethylstannyl)methyl]benzenesulfonamide.
Japanese Patent 57-072,905, assigned to Sumitomo, discloses insecticidal and herbicidal compounds of the formula: ##STR3## where R.sub.1, R.sub.2, and R.sub.3 are H or lower alkyl, or R.sub.2 and R.sub.3 taken together may form a quinoline ring; and